NP-MRD: Showing NP-Card for (4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid (NP0201503)

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Record Information

Version

2.0

Created at

2022-09-04 20:33:40 UTC

Updated at

2022-09-04 20:33:40 UTC

NP-MRD ID

NP0201503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid

Description

(4S)-4-({[(1S,2R,3aR)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-C-hydroxycarbonimidoyl)-4-oxo-1H,2H,3H,3aH,4H,5H,9bH-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. (4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid is found in Streptomyces albogriseolus. Based on a literature review very few articles have been published on (4S)-4-({[(1S,2R,3aR)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-C-hydroxycarbonimidoyl)-4-oxo-1H,2H,3H,3aH,4H,5H,9bH-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222332D          

 37 39  0  0  1  0            999 V2000
    4.5582   -3.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4719   -2.6790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8930   -2.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6075   -2.1171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6938   -1.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  4  0  0  0
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 20 36  1  0  0  0  0
  5 36  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042222332D          

 37 39  0  0  1  0            999 V2000
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  3  4  1  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 20 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@@H](N(C)[C@]2(C(O)=N[C@@H](CCC(O)=O)C(=O)C=C(C)C)C(=O)CC3=CC=CC=C3C12O)C(O)=NC

> <INCHI_IDENTIFIER>
InChI=1S/C26H33N3O8/c1-14(2)12-18(30)17(10-11-20(32)33)28-24(35)25-19(31)13-15-8-6-7-9-16(15)26(25,36)22(37-5)21(29(25)4)23(34)27-3/h6-9,12,17,21-22,36H,10-11,13H2,1-5H3,(H,27,34)(H,28,35)(H,32,33)/t17-,21+,22-,25-,26?/m0/s1

> <INCHI_KEY>
ZJWSUVTUVLTDNG-PWVHOQKMSA-N

> <FORMULA>
C26H33N3O8

> <MOLECULAR_WEIGHT>
515.563

> <EXACT_MASS>
515.226765035

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.20824960577804

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-({[(1S,2R,3aR)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-C-hydroxycarbonimidoyl)-4-oxo-1H,2H,3H,3aH,4H,5H,9bH-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid

> <JCHEM_LOGP>
-0.6327534230903243

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.9384334048070087

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.501495511373514

> <JCHEM_PKA_STRONGEST_BASIC>
11.89345071304711

> <JCHEM_POLAR_SURFACE_AREA>
169.32

> <JCHEM_REFRACTIVITY>
133.27619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-({[(1S,2R,3aR)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-C-hydroxycarbonimidoyl)-4-oxo-1H,2H,5H-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.509  -6.532   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       8.348  -5.001   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.593  -4.096   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.433  -2.564   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.000  -4.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.334  -3.952   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.495  -2.420   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.249  -1.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.478  -4.982   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.954  -3.518   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      15.010  -4.821   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.636  -3.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.168  -3.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.073  -4.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.447  -5.906   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.915  -6.067   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.289  -7.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.757  -7.635   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.131  -9.042   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.852  -6.389   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.082  -7.723   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.402  -9.229   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      10.542  -7.723   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       9.772  -9.057   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.232  -9.057   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.462 -10.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.922 -10.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.152 -11.724   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.152  -9.057   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.542 -10.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.082 -10.390   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.772 -11.724   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.542 -13.058   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.772 -14.391   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.082 -13.058   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      11.321  -6.228   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       9.987  -6.998   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   36                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11   20                                             
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    9   21   36                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   20    5   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(4S)-4-({[(1S,2R,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-C-hydroxycarbonimidoyl)-4-oxo-1H,2H,3H,3ah,4H,5H,9BH-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoate	Generator

Chemical Formula

C₂₆H₃₃N₃O₈

Average Mass

515.5630 Da

Monoisotopic Mass

515.22677 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@@H](N(C)[C@]2(C(O)=N[C@@H](CCC(O)=O)C(=O)C=C(C)C)C(=O)CC3=CC=CC=C3C12O)C(O)=NC

InChI Identifier

InChI=1S/C26H33N3O8/c1-14(2)12-18(30)17(10-11-20(32)33)28-24(35)25-19(31)13-15-8-6-7-9-16(15)26(25,36)22(37-5)21(29(25)4)23(34)27-3/h6-9,12,17,21-22,36H,10-11,13H2,1-5H3,(H,27,34)(H,28,35)(H,32,33)/t17-,21+,22-,25-,26?/m0/s1

InChI Key

ZJWSUVTUVLTDNG-PWVHOQKMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces albogriseolus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Tetralin
Indole or derivatives
Medium-chain fatty acid
Aralkylamine
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Amino fatty acid
Fatty acyl
Fatty acid
Benzenoid
N-alkylpyrrolidine
Unsaturated fatty acid
Alpha,beta-unsaturated ketone
Tertiary alcohol
Pyrrolidine
Enone
Acryloyl-group
Amino acid
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163116197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid (NP0201503)

MOL for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

3D MOL for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

3D SDF for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

3D-SDF for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

PDB for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

3D PDB for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

SMILES for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

INCHI for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

Structure for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)

3D Structure for NP0201503 ((4s)-4-({[(1s,2r,3ar)-9b-hydroxy-1-methoxy-3-methyl-2-(methyl-c-hydroxycarbonimidoyl)-4-oxo-1h,2h,5h-benzo[e]indol-3a-yl](hydroxy)methylidene}amino)-7-methyl-5-oxooct-6-enoic acid)